


Bonus!-Date a Friend's Sibling

by destinyofdreams



Series: 30 Day Cheesy Tropes Challenge [30]
Category: Supernatural
Genre: 30 Day Cheesy Tropes Challenge, Blind Date, Bonus Cheesy Trope, Fluff, M/M, Not Beta Read, like major fluff
Language: English
Status: Completed
Published: 2014-09-29
Updated: 2014-09-29
Packaged: 2018-02-19 06:16:52
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,926
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2377892
Author URL: https://archiveofourown.org/users/destinyofdreams/pseuds/destinyofdreams
Summary: <blockquote class="userstuff">
              <p>Sam and Gabriel have been interested in each other for years.  They're both home on break from school and want to finally start dating officially.  There's a catch, Gabriel cannot go on a date until Castiel has a date.</p>
            </blockquote>





	Bonus!-Date a Friend's Sibling

Sam paced the kitchen while Dean made breakfast.  They had had the discussion the previous night and Sam had still gotten a no from Dean.

“Just because you’re living ‘Taming of the Shrew’ doesn’t mean I want to get stuck with the shrew,” Dean countered as he flipped the pancakes.

“C’mon Dean.  Please.  Gabriel just back from Dartmouth and I am only here for break.  I don’t want to go back to Columbia a virgin Dean,” Sam pleaded.

“One, ew! I did not need to know that.  Two, you do realize you guys are just a few hours apart from each other right?”

“It’s different up there.  We have dorms that we share.”

“Get a hotel.”

“Dean,” Sam stretched his name into two syllables.

“Why can’t he go out on a date without his brother dating first?”

“His brother is home for the first time in three years and his family doesn’t want him to be alone,” Sam sat at the table as Dean served breakfast.

“Where was he was for three years?”

“Away,” Sam stated innocently.

“Uh uh.  If I am goin’ to consider this I need to know.”

“He was in a special program overseas,” Sam picked up his fork and stared intently at his plate.

“Special like the government may recruit him for a program? Or special like ‘One Flew Over the Cuckoo’s Nest’?” Dean asked as he poured them juice.

“Uh more like ‘Girl, Interrupted’.”

“Jesus Sam,” Dean sighed as he took his seat, “you can never just have something simple go on can you?  Fine.  Tell Kate I’ll take him out tomorrow night.”

“His name is Castiel.  I programmed his number into your phone.”

“He is the Kate to Gabe’s Bianca so he’ll be Kate,” Dean ended the conversation by shoveling a forkful of food into his mouth.

 

Dean finished the housework and sat down in front the television.

**Dean:  Hey Kate this is Dean.  I’m told that you and I have to get out of our brother’s hair.  I’ll be there tomorrow at 6 sharp.**

**_Cas: I think you may have the wrong number.  This is Castiel._ **

Dean rolled his eyes.

**Dean: No.  It was a joke.  Gabe is Bianca and you’re Katherine.  Ya know?  b/c of the situation.**

**_Cas: Oh.  A literature joke.  I see.  It is very funny now that I look at it. As you will have it Dean.  I will see you tomorrow at six sharp.  What attire should I wear?_ **

**Dean: Casual.  I’m not a dress up fancy type of guy.**

**_Cas: Alright.  Thank you for taking me out.  I know that I will enjoy myself from the way Sam and Gabriel talk about you.  I look forward to it._ **

**Dean: I hope it was all good things ;)**

**_Cas: It was._ **

**Dean: Good.**

Dean was shocked that he fell into an easy text conversation with Castiel.  An hour had passed before he realized it.  He let him know that he was ending the conversation and flipped on his favorite show.

That night Sam entered the house with a grin and plopped down at the counter while Dean made dinner.

“So I hear that Cas has a date and is super excited,” Sam smiled.

“Yeah.”

“I hear he was glued to his phone all afternoon chatting with a new friend that he would not tell Gabriel about,” Sam’s grin grew.

“Yeah,” Dean nodded as he cooked.

“Are you blushing?”

“Sam shut up will ya?”

“You’re going to like him.”

“We’ll see.  When are you and Gabe goin’ out on a date?”

“They want to see how you and Cas go over then he will be allowed out with me.”

“Then I should make the date suck,” Dean smirked.

“You can’t.  It isn’t in you Dean Winchester to have a bad date.”

Dean made a noncommittal sound as he plated their food.

<<<>>> 

Dean could not remember ever being as nervous about a date as he was when he pulled in front of the Novak house.  Dean checked his teeth and got out of the car.  He took a deep breath and rang the door bell.

“Deano!” Gabriel hugged him tight, “long time no see.  Come on in.”

“Hey Gabe.”

“Dean,” Sam stood as they entered the living room.

“What are you doin’ here?” Dean felt his nervousness double.

“I had to see my brother off on his first date in like a decade.”

“It hasn’t been that long.”

“I’ll go let Cassy know you’re here,” Gabriel trotted up the stairs.

“So you look nice,” Sam smiled as he sat back down.

“Thanks,” Dean looked down at his dark denim jeans and fitted tee under the vest.

“Dean,” a warm feminine voice called behind him.

“Mrs. Novak,” Dean hugged her and kissed her cheek, “so good to see you again.”

“You as well.  I am very pleased to hear you’re taking Castiel out.  I know you guys never met with him being in boarding school.  I promise he won’t be too much trouble,” Mrs. Novak chuckled.

“Can’t be any more than Gabriel right?” Dean smiled.

“Amen to that.  Mr. Novak wanted to be here but he got called to the office.”

“Father is always absent,” Gabriel said as he rushed down the stairs.

“Gabriel,” Mrs. Novak warned.

“Sorry mom.”

They chatted for a few while they waited for Castiel to come down.  They settled back into the living room.  Dean checked his watch and it was a minute to six when he heard Castiel’s footfalls.  Everyone went silent when he entered the room.  Dean swallowed hard.  Dean had remembered pictures of a chubby little dark haired boy with Gabriel and Michael in family photos.  The man that walked in the room had left that little boy far behind.  Dean approved immediately even if he seemed a little awkward.  Dean stood and the others followed. 

“Hey Cas.”

“You said six sharp.  Not ten ‘til,” Castiel brushed his bangs out of his face.

“Yeah.  Okay.  Let’s get outta here and leave your family to it,” Dean took his hand.

Castiel stared at his hand for a moment then nodded.

“Goodnight mother.  Make sure Gabriel stays out of my room please Sam.”

“Have a good night boys.”

Dean and Castiel were on the road before Dean spoke.

“They do realize we’re 30 right?”

“I think that they do but they assume we need coddling because we have been single for so long.  They are worried how you will take me knowing that I have been institutionalized,” Castiel spoke softly.

“Eh.  I’ve dated crazy before,” Dean teased, “just don’t pull a knife on me.  I will break your wrist.”

“Noted.  I should leave my pocket knife hooked safely.”

“You got jokes?  I like it,” Dean smiled as he headed to the restaurant.

“I have tons of jokes.  You will not get some of them.”

“Are you’re sayin’ you’re too smart for me to get your jokes?” Dean frowned.

“No.  They’re in Russian and Enochian.”

“Oh!  I will literally not get them,” Dean chuckled, “well Kate I think we’re gonna have a fine time tonight.”

Dean was surprised how much he did get along with Castiel.  Even with his offbeat humor and overly serious expression Dean felt himself falling.  He had not expected it and felt at odds with himself.  After dinner Dean took them to the shooting range.  He had planned it as a date that would make Castiel decline any other dates but got shocked.  Castiel not only enjoyed the shooting range but beat Dean’s score.  Apparently marksmanship was part of his boarding school curriculum. 

Castiel opened up and Dean felt himself being drawn in even more as he talked passionately about his new craft project.  Castiel loved to build and the boat he had started would be finished in time for the fall races.  Dean found the way Castiel animatedly talked endearing.  He smiled softly as he drove them to his last stop on their date.  It was a spot where the sky was clear and far enough from the city there was only limited light pollution.  Dean grabbed the blanket from the back and spread it out.  They started out in the upright position with Castiel pressed against his side and somehow ended up on their backs together while Dean named all the constellations.  Dean was shocked when Castiel pulled him in for a kiss.  Dean was quick to kiss back and pulled Castiel on top of him.

“Dean,” Castiel sighed against his lips.

“Sorry.  This date took a turn I wasn’t expecting,” Dean let him go.

“No it’s fine.  I just,” Castiel blushed and sat up, “I have never wanted to be with someone as much as I do you.  That is not the type of man I am.”

“Oh,” Dean smiled and sat up beside him, “I understand.  Don’t worry.  I don’t give it up on the first date.”

“That is good to know.  I’m safe from you then,” Castiel smiled the first big smile all night from him.

“I should get you home.  Your brother has already text me three times.”

“Very well.”

Dean smiled as Castiel’s hand gripped his while they drove back to the Novak house.  He learned that Castiel was searching for his own place since he would be permanently staying in town.  Dean offered to help him look and made a mental note to make sure it was close to his house. They pulled up in the driveway and Dean cut the engine.

“I had a great time Dean,” Castiel unbuckled and leaned across the seat.

“Me too.”

They kissed for a few minutes and the porch light turned on.  Gabriel walked out to the porch.

“No losing your virginity in a car Cassy!”

Castiel groaned and pulled back from Dean, “not a virgin Gabe!”

“Well that’s good to know,” Dean chuckled.

“Oh,” Castiel blushed, “that was not appropriate.”

“It’s alright.  I’m not either if it makes you feel better.  So no virtue to worry about,” Dean pulled him for another kiss.

“Cassy!”

“I hate that I’m not an only child.  I will see you around Dean.  I expect a text that you made it home safe,” Castiel said as he got out of the car.

“Of course.  See ya later Cas.”

Dean watched Castiel make it to the house and swat at Gabriel then headed home.  He got back and Sam was in the rocker with a stern look.  Dean was not sure where Sam had pulled the huge plastic curlers and the violet floral housecoat from but it worked.  It added to the matronly appeal.  Dean smiled.

“Do you have any idea what time it is young man?”  Sam’s lips twitched as a smile fought against his faux stern look.

“About one in the morning give or take,” Dean grinned.

“Wow you had a good night.”

“Yeah.  A really good night.  Cas is something else.”

“Thank you,” Sam jumped up and hugged him.

“No.  Thank you.  If it wasn’t for you I wouldn’t have met such a great guy,” Dean hugged him back, “no double dates before you even ask.”

“I’m gonna call Gabe.  See ya in the morning,” Sam bounced off to his room.

“You would think he was 16 and not 26,” Dean mumbled as he headed to his room.

Dean changed for bed and sent Castiel a text.  Dean smiled at the kitten picture Castiel sent back.  He was a goner.  Dean had gone out that night with expectations of a crash and burn date but instead found someone he genuinely liked and hoped for more.

**Author's Note:**

> YAY! Bonus! Again, thanks a bunch for being awesome and taking your time to read, comment and leave kudos! Have a fantastic day!


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